methyl 2-(1-H-indol-3-yl)ethylcarbamate
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 60℃; | 95% |
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating; | 94% |
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene for 3h; Inert atmosphere; Reflux; | 84% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 3.25h; Heating; | 90% |
With lithium aluminium tetrahydride | |
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating; Yield given; |
ethyl 2-(1H-indole-3-yl)ethylcarbamate
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating; | 89% |
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux; | 86% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Reflux; | 85% |
tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 24h; | 52% |
indole
oxalyl dichloride
methylamine
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
Stage #1: indole; oxalyl dichloride In tetrahydrofuran at 0 - 20℃; Stage #2: methylamine In tetrahydrofuran at 0 - 20℃; for 2h; Stage #3: With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Reflux; | 50% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 7h; Inert atmosphere; Reflux; | 42% |
Conditions | Yield |
---|---|
With dimethylsulfide borane complex In tetrahydrofuran for 48h; Heating; | A 29% B 24% C 36% |
methyl 2-(1-H-indol-3-yl)ethylcarbamate
A
[2-(1H-indol-3-yl)-ethyl]-methylamine
(±)-1,1'-dimethyl-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole
C
meso-Chimonanthine
Conditions | Yield |
---|---|
Stage #1: methyl 2-(1-H-indol-3-yl)ethylcarbamate With 2,2,2-trifluoroethanol; bis-[(trifluoroacetoxy)iodo]benzene at -30℃; Stage #2: With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene Heating; | A 9% B 13% C 30% D 23% |
N-(2-(1H-indol-3-yl)ethyl)-N,4-dimethylbenzenesulfonamide
aniline hydrochloride
aniline
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
With ethanol |
Conditions | Yield |
---|---|
at 320℃; under 12 Torr; |
(2-indol-3-yl-ethyl)-carbamic acid benzyl ester
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Heating; |
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / aq. NaOH / CHCl3 / 3 h / 20 °C 2: 89 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 81 percent / DIEA / tetrahydrofuran 2: 79 percent / lithium aluminum hydride / tetrahydrofuran / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / aq. NaOH / CHCl3 / 3 h 2: 89 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1.1: 100 percent / NaOH / H2O; CH2Cl2 / 0 °C 2.1: phenyliodine(III)bis(trifluoroacetate); CF3CH2OH / -30 °C 2.2: 9 percent / Red-Al / toluene / Heating View Scheme | |
Multi-step reaction with 2 steps 1: Et3N 2: LiAlH4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 84 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: 50 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOH; H2O / CHCl3 / 1 h 2: LiAlH4 / tetrahydrofuran / 24 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: LiAlH4; diethyl ether 2: 130 °C 3: LiAlH4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diethyl ether; phosphorus (III)-bromide View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: zinc chloride View Scheme |
tryptamine
chloroformic acid ethyl ester
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
Stage #1: tryptamine; chloroformic acid ethyl ester With sodium hydroxide In water at 20℃; for 3h; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Heating / reflux; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0 °C 2: water / 2 h / Cooling with ice 3: lithium aluminium tetrahydride / tetrahydrofuran / 7 h / Inert atmosphere; Reflux View Scheme |
indolyl-3-glyoxylyl chloride
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water / 2 h / Cooling with ice 2: lithium aluminium tetrahydride / tetrahydrofuran / 7 h / Inert atmosphere; Reflux View Scheme |
[2-(1H-indol-3-yl)-ethyl]-methylamine
di-tert-butyl dicarbonate
tert-butyl N-methyl-N-2-[(1H-indol-3-yl)-ethyl]carbamate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere; | 100% |
With triethylamine In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere; | 99% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 110℃; | 100% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
methyl chloroformate
methyl (2-(1H-indol-3-yl)ethyl)(methyl)carbamate
Conditions | Yield |
---|---|
With triethylamine In chloroform at 20℃; for 23h; | 99% |
With dmap; triethylamine In dichloromethane at 0℃; Inert atmosphere; | 68% |
With triethylamine Yield given; |
2-bromo-thiazole-5-carboxylic acid
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h; | 98% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
4-Nitrobenzenesulfonyl chloride
N-(2-(1H-indol-3-yl)ethyl)-N-methyl-4-nitrobenzenesulfonamide
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 97.5% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
5,5-diethoxypentanal
1-(4,4-Diethoxy-butyl)-2-methyl-2,3,4,9-tetrahydro-1H-β-carboline
Conditions | Yield |
---|---|
In toluene for 2h; Heating; | 97% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
Dimethyl 3-(methylthio)-1,2,4-triazine-5,6-dicarboxylate
Conditions | Yield |
---|---|
In methanol Heating; | 95% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
C17H22N2O3
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 95% |
5-phenylfuran-2-carbaldehyde
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
Stage #1: 5-phenylfuran-2-carbaldehyde; [2-(1H-indol-3-yl)-ethyl]-methylamine In methanol at 20℃; Molecular sieve; Stage #2: With sodium tetrahydroborate In methanol for 1h; Molecular sieve; | 95% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
2-(4-(benzyloxy)phenyl)acetyl chloride
Conditions | Yield |
---|---|
In dichloromethane for 1h; | 94.3% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
tris(3-methylbut-2-enyl)borane
Conditions | Yield |
---|---|
Stage #1: [2-(1H-indol-3-yl)-ethyl]-methylamine; tris(3-methylbut-2-enyl)borane at 120 - 130℃; for 4.5h; Stage #2: With sodium hydroxide In water | 94% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
(fluorenylmethoxy)carbonyl chloride
C26H24N2O2
Conditions | Yield |
---|---|
With sodium carbonate In dichloromethane; water at 20℃; for 0.25h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
In ethanol Heating; | 91% |
formic acid
[2-(1H-indol-3-yl)-ethyl]-methylamine
Nb-formyl-Nb-methyltryptamine
Conditions | Yield |
---|---|
Stage #1: formic acid With acetic anhydride at 60℃; for 1h; Stage #2: [2-(1H-indol-3-yl)-ethyl]-methylamine In dichloromethane at 20℃; for 1.5h; | 90% |
With acetic anhydride In diethyl ether |
[2-(1H-indol-3-yl)-ethyl]-methylamine
N-methyl-N-(4-carboxybutyryl)-tryptamine
Conditions | Yield |
---|---|
In benzene | 90% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
S-(3-phenylpropyl) 4-iodobenzenecarbothioate
C18H17IN2O
Conditions | Yield |
---|---|
With potassium phosphate; silver trifluoromethanesulfonate In acetonitrile at 70℃; for 16h; | 90% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
p-toluenesulfonyl chloride
N-(2-(1H-indol-3-yl)ethyl)-N,4-dimethylbenzenesulfonamide
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere; | 90% |
With dmap; triethylamine In dichloromethane at 0℃; Inert atmosphere; | 71% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 5h; | 90% |
phthalic anhydride
[2-(1H-indol-3-yl)-ethyl]-methylamine
N,N'-bis[2-(1H-indol-3-yl)-ethyl]-N,N'-dimethyl-phthalamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide | 89% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
4-methoxy-3-(4-(2,2,2-trichloro-acetyl)piperazin-1-yl)benzene-1-sulfonylchloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 25℃; | 88.5% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
(2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate
Conditions | Yield |
---|---|
With potassium tert-butylate In methanol at 5℃; for 3h; Temperature; Reagent/catalyst; | 88% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
carbon monoxide
2,9-dihydro-2-methyl-1H-pyrido[3,4-b]indol-1-one
Conditions | Yield |
---|---|
With oxygen; copper diacetate; palladium diacetate In toluene at 110℃; under 760.051 Torr; for 24h; Schlenk technique; | 88% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
N,N-dimethyl-2-(3-cyano-pyridin-4-yl)etheneamine
4-((E)-2-{[2-(1H-Indol-3-yl)-ethyl]-methyl-amino}-vinyl)-nicotinonitrile
Conditions | Yield |
---|---|
With o-toluenesulfonic acid In toluene for 72h; Heating; | 87% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
With chloroamine-T; potassium iodide In chloroform for 0.0833333h; | 87% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
With triethylsilane; trifluoroacetic acid at 60℃; for 4h; | 87% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
carbon monoxide
Strychnocarpine
Conditions | Yield |
---|---|
With oxygen; copper diacetate; palladium diacetate In toluene at 110℃; for 6h; | 86% |
With oxygen; copper diacetate; palladium diacetate In toluene at 80℃; under 760.051 Torr; for 6h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; | 86% |
[2-(1H-indol-3-yl)-ethyl]-methylamine
Conditions | Yield |
---|---|
With sodium hydroxide; [131I]-sodium iodide; chloroamine-T In chloroform for 0.05h; | 85.6% |
The CAS register number of 3-(2-Methylaminoethyl)indole is 61-49-4. It also can be called as N(omega)-Methyltryptamine and the IUPAC name about this chemical is 2-(1H-indol-3-yl)-N-methylethanamine. The molecular formula about this chemical is C11H14N2 and the molecular weight is 174.24. It belongs to the following product categories, such as Tryptamines; Heterocyclic Compounds and so on. When you are using it, please avoid contact with skin and eyes.
Physical properties about 3-(2-Methylaminoethyl)indole are: (1)ACD/LogP: 1.52; (2)ACD/LogD (pH 5.5): -1.58; (3)ACD/LogD (pH 7.4): -1.42; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 8.17Å2; (12)Index of Refraction: 1.621; (13)Molar Refractivity: 56.3 cm3; (14)Molar Volume: 160 cm3; (15)Polarizability: 22.32x10-24cm3; (16)Surface Tension: 45.2 dyne/cm; (17)Enthalpy of Vaporization: 57.93 kJ/mol; (18)Boiling Point: 336.2 °C at 760 mmHg; (19)Vapour Pressure: 0.000114 mmHg at 25°C.
Preparation: this chemical can be prepared by N-(2-indol-3-yl-ethyl)-formamide. This reaction will need reagent LiAlH4.
Uses of 3-(2-Methylaminoethyl)indole: it can be used to produce 2-iodo-N-methyltryptamine. This reaction will need reagent aq. chloramine-T, KI and solvent CHCl3 with reaction time of 5 min. The yield is about 87%.
You can still convert the following datas into molecular structure:
(1)SMILES: c1cccc2c1c(cn2)CCNC
(2)InChI: InChI=1/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3
(3)InChIKey: NCIKQJBVUNUXLW-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3
(5)Std. InChIKey: NCIKQJBVUNUXLW-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 158mg/kg (158mg/kg) | BEHAVIORAL: EXCITEMENT | Journal of Toxicology and Environmental Health. Vol. 1, Pg. 515, 1976. |
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